Curable compositions and abrasive articles therefrom

ABSTRACT

A curable composition comprises: blocked polyisocyanate, curative, and a crosslinked copolymer of monomers comprising at least one free-radically polymerizable carboxylic acid and at least one of an alkyl or alkaryl(meth)acrylate. Methods of making the curable compositions and their use in the manufacture of abrasive articles are also disclosed.

TECHNICAL FIELD

The present invention relates to curable compositions. The presentinvention also relates to curable compositions used in the manufactureof abrasive articles.

BACKGROUND

Polyurethanes (i.e., polymers containing urethane and/or urea linkagesin the backbone chain) are widely used as binder materials for manyapplications due to their physical properties (e.g., strength,elongation, and/or toughness). Many polyurethane binders are formed bycuring (i.e., at least partially polymerizing and/or crosslinking)polyurethane precursors.

For some applications in which polyurethane binders are used (e.g.,applications in which the polyurethane may rub against a workpiece), itis desirable to reduce the coefficient of friction of the binder toprevent wear of the binder and/or transfer of the binder to a workpiece(i.e., smearing). The reduction of smearing may be particularlyimportant in the manufacture and use of abrasive articles.

It would be desirable to have curable compositions that are useful asbinder precursors. Alternatively, or in addition, it would also bedesirable if such curable compositions could be cured to provide bindershaving one or more physical properties of polyurethanes while having alow coefficient of friction and/or tendency to smear.

SUMMARY

In one aspect, the present invention provides a curable compositioncomprising:

-   -   blocked polyisocyanate;    -   curative; and    -   a crosslinked copolymer of monomers comprising at least one        free-radically polymerizable carboxylic acid and at least one of        an alkyl or alkaryl(meth)acrylate, wherein at least one of the        alkyl or alkaryl (meth)acrylate has from 11 carbon atoms to 34        carbon atoms.

In another aspect, the present invention provides a curable compositionpreparable from components comprising:

-   -   blocked polyisocyanate;    -   curative; and    -   a crosslinked copolymer of monomers comprising at least one        free-radically polymerizable carboxylic acid and at least one of        an alkyl or alkaryl(meth)acrylate, wherein at least one of the        alkyl or alkaryl (meth)acrylate has from 11 carbon atoms to 34        carbon atoms.

In another aspect, the present invention provides a compositioncomprising a polymerized reaction product of components comprising:

-   -   blocked polyisocyanate;    -   curative; and    -   a crosslinked copolymer of monomers comprising at least one        free-radically polymerizable carboxylic acid and at least one of        an alkyl or alkaryl(meth)acrylate, wherein at least one of the        alkyl or alkaryl (meth)acrylate has from 11 carbon atoms to 34        carbon atoms.

In another aspect, the present invention provides a compositioncomprising a polymerized reaction product of a curable compositionpreparable from components comprising:

-   -   blocked polyisocyanate;    -   curative; and    -   a crosslinked copolymer of monomers comprising at least one        free-radically polymerizable carboxylic acid and at least one of        an alkyl or alkaryl(meth)acrylate, wherein at least one of the        alkyl or alkaryl (meth)acrylate has from 11 carbon atoms to 34        carbon atoms.

In another aspect, the present invention provides a method for making acurable composition comprising mixing components comprising:

-   -   blocked polyisocyanate;    -   curative; and    -   a crosslinked copolymer of monomers comprising at least one        free-radically polymerizable carboxylic acid and at least one of        an alkyl or alkaryl (meth)acrylate, wherein at least one of the        alkyl or alkaryl(meth)acrylate has from 11 carbon atoms to 34        carbon atoms.

In another aspect, the present invention provides an abrasive articlecomprising abrasive particles and a polymerized reaction product of acurable composition according to the present invention.

In another aspect, the present invention provides a method of abrading aworkpiece comprising:

providing an abrasive article comprising:

-   -   abrasive particles and a polymerized reaction product according        to the present invention; and

frictionally contacting at least one abrasive particle with at least aportion of the surface of the workpiece; and

moving at least one of the at least one abrasive particle or theworkpiece relative to the other to abrade at least a portion of thesurface.

In another aspect, the present invention provides an abrasive articlecomprising abrasive particles and a polymerized reaction product of acurable composition according to the present invention.

Curable compositions prepared in accordance with the present inventionmay typically be cured to form binders having one or more physicalproperties of polyurethanes while having a low coefficient of frictionand/or tendency to smear. Useful abrasive articles, which may be madewith curable compositions according to the present invention, include,for example, coated abrasive articles, nonwoven abrasive articles, andbonded abrasive articles.

BRIEF DESCRIPTION OF THE DRAWING

FIGS. 1 and 2 are cross-sectional views of exemplary coated abrasivearticles according to the present invention;

FIG. 3 a is a perspective view of an exemplary nonwoven abrasive articleaccording to the present invention;

FIG. 3 b is an enlarged view of a region of the nonwoven abrasivearticle shown in FIG. 3 a;

FIG. 4 is a perspective view of an exemplary bonded abrasive articleaccording to the present invention;

FIG. 5 is a side view of an exemplary unitary brush according to thepresent invention; and

FIG. 6 is a front plan view of another exemplary unitary brush accordingto the present invention.

DETAILED DESCRIPTION

Curable compositions according to present invention comprise blockedpolyisocyanate, curative, and a crosslinked copolymer of monomerscomprising a free-radically polymerizable carboxylic acid and at leastone of an alkyl or alkaryl (meth)acrylate, wherein at least one of thealkyl or alkaryl(meth)acrylate has from 11 carbon atoms to 34 carbonatoms.

As used herein, the term “blocked polyisocyanate” refers to either asingle blocked polyisocyanate or a mixture of two or more blockedpolyisocyanates; the term “curative” refers to either a single curativeor a mixture of two or more curatives; and the term “(meth)acryl”encompasses “acryl” and/or “methacryl” (e.g., “(meth)acrylate”encompasses acrylate and/or methacrylate). Further, numerical rangesrecited herein are inclusive of their endpoints, unless otherwisespecified.

Useful blocked polyisocyanates include polyisocyanates (sometimesreferred to in the art as “urethane prepolymers”) wherein at least some(e.g., substantially all) of the isocyanate groups have been reacted(i.e., blocked) with a compound (i.e., blocking agent) that forms anadduct with isocyanate groups. Typically, the adduct is substantiallyunreactive to isocyanate reactive compounds (e.g., amines, alcohols,thiols, etc.) under ambient conditions (e.g., temperatures in a range offrom about 20° C. to about 25° C.), but upon application of sufficientthermal energy in the presence of curative, the adduct typically reactswith the curative to form a covalent bond. Procedures and materials forblocking polyisocyanates are well known in the art, and are described,for example, by D. A. Wicks and Z. W. Wicks, Jr. in “Blocked isocyanatesIII: Part A. Mechanisms and chemistry”, Progress in Organic Coatings,vol. 36(1999), Elsevier Science, New York, pages 148-172;and in “Blockedisocyanates III Part B: Uses and applications of blocked isocyanates”,Progress in Organic Coatings, vol. 41(2001), Elsevier Science, New York,pages 1-83, the disclosures of which are incorporated herein byreference.

Exemplary blocking agents include ketoximes (e.g., 2-butanone oxime);lactams (e.g., epsiloncaprolactam); malonic esters (e.g., dimethylmalonate and diethyl malonate); pyrazoles (e.g., 3,5-dimethylpyrazole);alcohols including tertiary alcohols (e.g., t-butanol or2,2-dimethylpentanol), phenols (e.g., alkylated phenols), and mixturesof alcohols as described, for example in U.S. Pat. No. 6,288,176B1(Hsieh et al.), the disclosure of which is incorporated herein byreference.

Useful polyisocyanates include, for example, aliphatic polyisocyanates(e.g., hexamethylene diisocyanate or trimethylhexamethylenediisocyanate); alicyclic polyisocyanates (e.g., hydrogenated xylylenediisocyanate or isophorone diisocyanate); aromatic polyisocyanates(e.g., tolylene diisocyanate or 4,4′-diphenylmethane diisocyanate);adducts of any of the foregoing polyisocyanates with a polyhydricalcohol (e.g., a diol, low molecular weight hydroxyl group-containingpolyester resin, water, etc.); adducts of the foregoing polyisocyanates(e.g., isocyanurates, biurets); and mixtures thereof.

Useful commercially available polyisocyanates include, for example,those available under the trade designation “ADIPRENE” from UniroyalChemical Company, Middlebury, Connecticut (e.g., “ADIPRENE L 0311”,“ADIPRENE L 100”, “ADIPRENE L 167”, “ADIPRENE L 213”, “ADIPRENE L 315”,“ADIPRENE L 680”, “ADIPRENE LF 1800A”, “ADIPRENE LF 600D”, “ADIPRENE LFP1950A”, “ADIPRENE LFP 2950A”, “ADIPRENE LFP 590D”, “ADIPRENE LW 520”,and “ADIPRENE PP 1095”); polyisocyanates available under the tradedesignation “MONDUR” from Bayer Corporation, Pittsburgh, Pennsylvania(e.g., “MONDUR 1437”, “MONDUR MP-095”, or “MONDUR 448”); andpolyisocyanates available under the trade designations “AIRTHANE” and“VERSATHANE” from Air Products and Chemicals, Allentown, Pa. (e.g.,“AIRTHANE APC-504”, “AIRTHANE PST-95A”, “AIRTHANE PST-85A”, “AIRTHANEPET-91A”, “AIRTHANE PET-75D”, “VERSATHANE STE-95A”, “VERSATHANESTE-P95”, “VERSATHANE STS-55”, “VERSATHANE SME-90A”, and “VERSATHANEMS-90A”).

Exemplary useful commercially available blocked polyisocyanates includethose marketed by Uniroyal Chemical Company under the trade designations“ADIPRENE BL 11”, “ADIPRENE BL 16”, “ADIPRENE BL 31”, “ADIPRENE BL 40”,“ADIPRENE BL 45”, “ADIPRENE BL 46”, “ADIPRENE BLM 500”, “ADIPRENE BLP60”, or “ADIPRENE BLP 65”, and blocked polyisocyanates marketed byBaxenden Chemicals, Ltd., Accrington, England available under the tradedesignation “TRIXENE” (e.g., “TRIXENE BI 7986”, “TRIXENE BI 7985”,“TRIXENE BI 7951”, “TRIXENE BI 7950”, “TRIXENE BI 7960”, or “TRIXENE BI7770”).

In some embodiments according to the present invention, the blockedisocyanate may have the formula:

wherein n is an integer greater than or equal to 1, for example, n maybe in a range of from 7to 25, although higher and lower values of n mayalso be useful. Blocked isocyanates described by this formula include,for example, those marketed under the trade designation “ADIPRENE BL11”, “ADIPRENE BL 16”, “ADIPRENE BL 31” by Uniroyal Chemical Company.

Typically, the amount of blocked isocyanate is in a range of from 5percent by weight to 90 percent by weight, based on the total weight ofthe curable composition, although higher and lower other amounts may beused. For example, blocked isocyanate may be present in an amount in arange of from 10 percent by weight to 80 percent by weight, and/or in arange of from about 40 percent by weight to about 80 percent by weight,based on the total weight of the curable composition.

Typically, a curative is a substance having a plurality of activehydrogen sites such as may be provided by —OH, —NH₂, —SH groups, or thelike. Useful curatives include, for example, polyamines (e.g.,4,4′-methylenedianiline, 3-aminomethyl-3,5,5-trimethylcyclohexylamine(i.e., isophoronediamine), trimethylene glycol di-p-aminobenzoate,bis(o-aminophenylthio)ethane, and 4,4′-methylenebis(dimethylanthranilate)), and polyols (e.g., 1,4-butanediol, 1,6-hexanediol,pentaerythritol). Mixtures of polyamines, polyols, and/or mixtures ofpolyamines with polyols may be useful, for example, to modify reactionrates as required by the intended use.

The curative may comprise an aromatic diamine such as for examplebis(4-amino-3-ethylphenyl)methane (marketed under the trade designation“KAYAHARD AA” by Nippon Kayaku Company, Ltd., Tokyo, Japan) orbis(4-amino-3,5-diethylphenyl)methane (marketed under the tradedesignation “LONZACURE M-DEA” by Lonza, Ltd., Basel, Switzerland).Typically, curative should be present in an amount effective (i.e., aneffective amount) to cure the blocked polyisocyanate to the degreerequired by the intended application; for example, in a stoichiometricratio of curative to blocked isocyanate in a range of from 0.75 to 1.25and/or in a range of from 0.95 to 1.190, although stoichiometric ratiosoutside this range may also be used.

Useful free-radically polymerizable carboxylic acids have at least onecarboxyl group covalently bonded to a polymerizable carbon-carbon doublebond. As used herein, the term “carboxylic acid” encompasses thecorresponding conjugate base (i.e., carboxylate). Exemplaryfree-radically polymerizable carboxylic acids include itaconic acid,(meth)acrylic acid, maleic acid, fumaric acid, salts of the foregoing,and mixtures thereof. The phrase “copolymer of monomers comprising” isrefers to the structure of the copolymer rather than any particularmethod of preparing the copolymer. For example, the copolymer may beprepared using a monomer (e.g., maleic anhydride) that on hydrolysis(before or after co-polymerization) results in a free-radicallypolymerizable carboxylic acid. In order to ensure good swellability ofthe crosslinked copolymer with water, the acid content typically fallsin a range of from about 40 percent to about 90 percent by weight (e.g.,in a range of from 50 to 70 percent by weight) of the crosslinkedcopolymer, although acid content values outside this range may also byuseful.

Useful alkyl and alkaryl(meth)acrylates have from 11 carbon atoms to 34carbon atoms, and may be linear or branched. Examples of useful alkyland alkaryl (meth)acrylates include octyl(meth)acrylate,isooctyl(meth)acrylate, octadecyl (meth)acrylate,tridecyl(meth)acrylate, and nonylphenyl acrylate.

Optionally, additional co-monomers (e.g., (meth)acrylamide,butyl(meth)acrylate) may be included in the crosslinked copolymer.

Crosslinking is typically accomplished by inclusion of a monomer havingmultiple free-radically polymerizable groups (i.e., polyfunctionalmonomer) in the monomer mixture prior to copolymerization, althoughother methods may be used. Useful polyfunctional monomers are well knownand include, for example, pentaerythritol trivinyl ether, ethyleneglycol divinyl ether, and 1,6-hexanediol diacrylate. The amount ofcrosslinking desired will determine the amount of polyfunctional monomerused. In order to ensure good swellability with water, the crosslinkdensity should typically be kept at very low level, with value of M_(c)the average molecular weight of segments between crosslinks of greaterthan 1000g/mole, greater than 2000 g/mole, and/or greater than 3000g/mole.

Examples of useful commercially available crosslinked copolymersinclude, for example, those marketed by Noveon, Inc., Cleveland, Ohiounder the trade designations “CARBOPOL” and “PEMULEN” (e.g., “CARBOPOL674 POLYMER”, “CARBOPOL 676 POLYMER”, “° CARBOPOL 934 POLYMER”,“CARBOPOL 940 POLYMER”, “CARBOPOL 941 POLYMER”, “CARBOPOL 980 POLYMER ”,“CARBOPOL 981 POLYMER”, “CARBOPOL 1342 POLYMER”, “CARBOPOL 1610POLYMER”, “PEMULEN 1621 RESIN ”, “PEMULEN 1622 RESIN”, “CARBOPOL 1623POLYMER”, “CARBOPOL 2984 POLYMER”, and “CARBOPOL 5984 POLYMER”).

The crosslinked copolymer may be present in the curable compositionand/or cured composition in an amount of from at least 0.001 percent byweight, at least 0.1 percent by weight, at least 1 percent by weight, atleast 5 percent by weight, up to about 10 percent by weight, 20 percentby weight, 30 percent by weight, 40 percent by weight, or even higher,based on the total weight of the curable composition.

Typically, the crosslinked copolymer is in the form of particles, forexample having an average dry (i.e., non-swelled) particle size in arange of from about 0.1 micrometers to about 10 micrometers, or in arange of from about 2 micrometers to about 7 micrometers, althoughlarger and smaller particles may also be used.

Optionally, curable compositions according to the present invention maycontain at least one organic solvent. The amount of organic solvent istypically chosen based on considerations such as, for example, thedesired viscosity of the curable composition. Exemplary classes oforganic solvents include alkanes, alcohols, ketones, esters, and ethers

In some embodiments according to the present invention, curablecompositions are free of added filler and/or grinding aid. Such curablecompositions may be useful, for example, for preparing abrasive articlesthat exhibit abrasive properties comparable to commercially availableabrasive articles with binders that include fillers and/or grindingaids. As used herein, the term “free of added filler and/or grindingaid” means that such materials are either wholly absent or present insufficiently small amounts that they do not exhibit a change of morethan five percent in mechanical (i.e., tensile stress and elongation) orabrasive properties (i.e., cut and wear) of the cured composition.

Curable compositions according to the present invention may optionallyinclude at least one, optionally curable, additional polymer or polymerprecursor. Exemplary optional additional polymers and/or polymerprecursors include phenolic resins, urea-formaldehyde resins,melamine-formaldehyde resins, urethane resins, acrylate resins,polyester resins, aminoplast resins having pendant alpha,beta-unsaturated carbonyl groups, epoxy resins, acrylated urethanes,acrylated epoxies, and combinations thereof.

Optionally, curable compositions may be mixed with and/or include one ormore additives. Exemplary additives include fillers, coupling agents,plasticizers, surfactants, lubricants, colorants (e.g., pigments),bactericides, fungicides, grinding aids, and antistatic agents.

Curable compositions according to the present invention may be prepared,for example, by heating, individually or in combination, blockedpolyisocyanate and curative to a temperature in a range of from about50° C. to about 70° C., and combining them. The exact temperature is notcritical as long as the combination of blocked polyisocyanate andcurative forms a reasonably uniform mixture. If using low viscositycomponents, the curable composition may be prepared without heating,although heating may be used.

The blocked polyisocyanate, acidic copolymer, and optional components(e.g., organic solvent, curative, other additives) may be combined usingwell-known mixing techniques (e.g., a motorized mixer having a propellerblade).

In some aspects according to the present invention, abrasive particlesmay be added to curable compositions of the present invention.

Curable compositions according to the invention may be applied to asubstrate by any method known for applying a composition includingspraying, roll coating, gravure coating, dip coating, curtain coating,die coating, and the like.

Once applied to a substrate, curable compositions according to thepresent invention may be at least partially dried to remove optionalorganic solvent. Drying may be accomplished, for example, byevaporation, preferably at elevated temperature (i.e., above ambienttemperature, for example, in a range of from about 50° C. to about 120°C.). After sufficient optional organic solvent has been removed, theremaining components are typically at least partially cured byapplication of thermal energy (e.g., at a temperature greater than about120° C., although other curing temperatures may be utilized). Typically,drying and curing may be performed sequentially, or as a single processstep. Exemplary useful sources of thermal energy includes ovens, heatedrolls, and/or infrared lamps. If desired, further application of thermalenergy (e.g., by heating to a higher temperature) may also be desirableto improve binder properties.

Curable compositions according to the present invention may be used toprepare protective coatings, binders (e.g., for nonwoven articles), andthe like. Further, curable compositions according to the presentinvention may be used to prepare abrasive articles such as, for example,coated abrasive articles, nonwoven abrasive articles, bonded abrasivearticles, and/or abrasive brushes.

In general, coated abrasive articles have abrasive particles secured toa backing. More typically, coated abrasive articles comprise a backinghaving two major opposed surfaces and an abrasive coat secured to amajor surface. The abrasive coat is typically comprised of abrasiveparticles and a binder, wherein the binder serves to secure the abrasiveparticles to the backing.

Suitable abrasive particles include any abrasive particles known in theabrasive art. Exemplary useful abrasive particles include fused aluminumoxide based materials such as aluminum oxide, ceramic aluminum oxide(which may include one or more metal oxide modifiers and/or seeding ornucleating agents), and heat-treated aluminum oxide, silicon carbide,co-fused alumina-zirconia, diamond, ceria, titanium diboride, cubicboron nitride, boron carbide, garnet, flint, emery, sol-gel derivedabrasive particles, and blends thereof. Preferably, the abrasiveparticles comprise fused aluminum oxide, heat-treated aluminum oxide,ceramic aluminum oxide, silicon carbide, alumina zirconia, garnet,diamond, cubic boron nitride, sol-gel derived abrasive particles, ormixtures thereof.

The abrasive particles may be in the form of, for example, individualparticles, abrasive composite particles, agglomerates (includingerodible agglomerates), and mixtures thereof (e.g., having the same ordifferent size and/or composition).

The abrasive particles typically have an average diameter of from about0.1 micrometers to about 2000 micrometers, more preferably from about 1micrometers to about 1300 micrometers, although other particles havingother diameters can be used. Coating weights for the abrasive particlesmay depend on, for example, the type of abrasive article (e.g., coatedabrasive article or nonwoven abrasive article), the process for applyingthe abrasive particles, and the size of the abrasive particles, buttypically range from about 5 grams per square meter (g/m²) to about 1350g/m².

In one exemplary embodiment of a coated abrasive article, the abrasivecoat may comprise a make coat, optional size coat, and abrasiveparticles. Referring now to FIG. 1, exemplary coated abrasive article100 has backing 120 and abrasive coat 130 according to the presentinvention. Abrasive coat 130, in turn, includes abrasive particles 140secured to major surface 170 of backing 120 by make coat 150 andoptional size coat 160.

In making such a coated abrasive article, a make coat comprising a firstbinder precursor is applied to a major surface of the backing. Abrasiveparticles are then at least partially embedded into the make coat (e.g.,by electrostatic coating), and the first binder precursor is at leastpartially cured to secure the particles to the make coat. If utilized,an optional size coat comprising a second binder precursor (which may bethe same or different from the first binder precursor) is then appliedover the make coat and abrasive particles, followed by curing the binderprecursors.

Optionally, coated abrasive articles may further comprise, for example,a backsize (i.e., a coating on the major surface of the backing oppositethe major surface having the abrasive coat), a presize or a tie layer(i.e., a coating between the abrasive coat and the major surface towhich the abrasive coat is secured), and/or a saturant which coats bothmajor surfaces of the backing. Coated abrasive articles may furthercomprise a supersize covering the abrasive coat. If present, thesupersize typically includes grinding aids and/or anti-loadingmaterials.

In another exemplary embodiment of a coated abrasive article accordingto the present invention, the abrasive coat may comprise a cured slurryof a binder precursor and abrasive particles. Referring to FIG. 2,exemplary coated abrasive article 200 has backing 220 and abrasive coat230. Abrasive coat 230, in turn, includes abrasive particles 240 andbinder 245 according to the present invention.

In making such a coated abrasive article, a slurry comprising a firstbinder precursor and abrasive particles is typically applied to a majorsurface of the backing, and the binder precursor is then at leastpartially cured. Curable compositions according to the present inventionmay be included in binder precursors used to prepare one or more of theabovementioned layers and coatings of coated abrasive articles.

Coated abrasive articles according to the present invention may beconverted, for example, into belts, rolls, discs (including perforateddiscs), and/or sheets. For belt applications, two free ends of theabrasive sheet may be joined together using known methods to form aspliced belt.

Further description of techniques and materials for making coatedabrasive articles may be found in, for example, U.S. Pat. No. 4,314,827(Leitheiser et al.); U.S. Pat. No. 4,518,397 (Leitheiser et al.); U.S.Pat. No. 4,588,419 (Caul et al.); U.S. Pat. No. 4,623,364 (Cottringer etal.); U.S. Pat. No. 4,652,275 (Bloecher et al.); U.S. Pat. No. 4,734,104(Broberg); U.S. Pat. No. 4,737,163 (Larkey); U.S. Pat. No. 4,744,802(Schwabel); U.S. Pat. No. 4,751,137 (Tumey et al.); U.S. Pat. No.4,770,671 (Monroe et al.); U.S. Pat. No. 4,799,939 (Bloecher et al.);U.S. Pat. No. 4,881,951 (Wood et al.); U.S. Pat. No. 4,927,431 (Buchananet al.); 5,498,269 (Larmie); U.S. Pat. No. 5,011,508 (Wald et al.); U.S.Pat. No. 5,078,753 (Broberg et al.); U.S. Pat. No. 5,090,968 (Pellow);U.S. Pat. No. 5,108,463 (Buchanan et al.); U.S. Pat. No. 5,137,542(Buchanan et al.); U.S. Pat. No. 5,139,978 (Wood); U.S. Pat No.5,152,917 (Pieper et al.); U.S. Pat. No. 5,201,916 (Berg et al.); U.S.Pat. No. 5,203,884 (Buchanan et al.); U.S. Pat. No. 5,227,104 (Bauer);U.S. Pat. No. 5,328,716 (Buchanan); U.S. Pat. No. 5,366,523 (Rowenhorstet al.); U.S. Pat. No. 5,378,251 (Culler et al.); U.S. Pat. No.5,417,726 (Stout et al.); U.S. Pat. No. U.S. Pat. No. 5,429,647(Larmie); U.S. Pat. No. 5,436,063 (Follett et al.); U.S. Pat. No.5,490,878 (Peterson et al.); U.S. Pat. No. 5,492,550 (Krishnan et al.);U.S. Pat. No. 5,496,386 (Broberg et al.); U.S. Pat. No. 5,520,711(Helmin); 5,549,962 (Holmes et al.); U.S. Pat. No. 5,551,963 (Larmie);U.S. Pat. No. 5,556,437 (Lee et al.); U.S. Pat. No. 5,560,753 (Buchananet al.); U.S. Pat. No. 5,573,619 (Benedict et al.); U.S. Pat. No.5,609,706 (Benedict et al.); U.S. Pat. No. 5,672,186 (Chesley et al.);U.S. Pat. No. 5,700,302 (Stoetzel et al.); U.S. Pat. No. 5,942,015(Culler et al.); 5,954,844 (Law et al.); U.S. Pat. No 5,961,674(Gagliardi et al.); U.S. Pat. No. 5,975,988 (Christianson); U.S. Pat.No. 6,059,850 (Lise et al.); and U.S. Pat. No. 6,261,682 (Law), thedisclosures of which are incorporated herein by reference.

Nonwoven abrasive articles typically include a porous (e.g., a loftyopen porous) polymer filament structure having abrasive particles bondedthereto by a binder. An exemplary embodiment of a nonwoven abrasivearticle according to the present invention is shown in FIGS. 3 a and 3b, wherein lofty open low-density fibrous web 300 is formed of entangledfilaments 310 impregnated with binder 320 according to the presentinvention. Abrasive particles 340 are dispersed throughout fibrous web300 on exposed surfaces of filaments 310. Binder resin 320 uniformlycoats portions of filaments 310 and forms globules 350 which mayencircle individual filaments or bundles of filaments, adhere to thesurface of the filament and/or collect at the intersection of contactingfilaments, providing abrasive sites throughout the nonwoven abrasivearticle.

The fiber web may comprise continuous filaments (e.g., a spunbond fiberweb) and/or staple fibers that may be crimped and/or entangled with oneanother. Exemplary fibers include polyester fibers, polyamide fibers,and polyaramid fibers.

The fiber web may, optionally, be affixed (i.e., secured) to a backing,for example, by needletacking, stitchbonding, and/or adhesive bonding(e.g., using glue or a hot melt adhesive).

Binders and binder precursors (including curable compositions accordingto the present invention), backings, abrasive particles, optionaladditives, and optional layers set forth hereinabove for inclusion incoated abrasive articles may also be utilized in nonwoven abrasivesaccording to the present invention.

Nonwoven abrasive articles according to the invention may be convertedto a variety of useful forms including, for example, sheets, discs,belts, rolls, wheels, hand pads, cleaning brushes, and blocks.

Further description of techniques and materials for making nonwovenabrasive articles may be found in, for example, U.S. Pat. No. 2,958,593(Hoover et al.); U.S. Pat. No. 4,018,575 (Davis et al.); U.S. Pat. No.4,227,350 (Fitzer); U.S. Pat. No. 4,331,453 (Dau et al.); U.S. Pat.4,609,380 (Barnett et al.); U.S. Pat. No. 4,991,362 (Heyer et al.); U.S.Pat. No. 5,554,068 (Carr et al.); U.S. Pat. No. 5,712,210 (Windisch etal.); U.S. Pat. No. 5,591,239 (Edblom et al.); U.S. Pat. No. 5,681,361(Sanders); U.S. Pat. No. 5,858,140 (Berger et al.); U.S. Pat. No.5,928,070 (Lux); U.S. Pat. No. 6,017,831 (Beardsley et al.); U.S. Pat.No. 6,207,246 (Moren et al.); and U.S. Pat. No. 6,302,930 (Lux), thedisclosures of which are incorporated herein by reference.

Bonded abrasive articles typically include a shaped mass of abrasiveparticles held together by a binder. Referring now to FIG. 4, anexemplary embodiment of a bonded abrasive article according to thepresent invention has the form of grinding wheel 400, wherein abrasiveparticles 440 are held together by binder 420 according to the presentinvention to form a shaped mass mounted on hub 430.

In one method, bonded abrasive articles may be formed by preparing amixture of abrasive particles in a binder precursor, shaping the mixture(e.g., using a mold), and curing the binder precursor to form a binder.In one embodiment according to the present invention (e.g., a vitreousbonded abrasive article), the binder may be subsequently removed bypyrolysis.

Bonded abrasive articles according to the present invention may have anyform useful as an abrasive article such as, for example, a wheel (e.g.,grinding wheel, polishing wheel, cutoff wheel), a honing stone, a belt,mounted points, or other conventional bonded abrasive shape.

Further details regarding bonded abrasive articles may be found in, forexample, U.S. Pat. No. 4,800,685 (Haynes et al.); U.S. Pat. No.4,898,597 (Hay et al.); U.S. Pat. No. 4,933,373 (Moren); U.S. Pat. No.5,282,875 (Wood et al.), the disclosures of which are incorporatedherein by reference.

Curable compositions according to the present invention are also usefulas binder precursors for the preparation of abrasive brushes such asflap brushes as described, for example, in U.S. Pat. No. 5,554,068 (Carret al.), and unitary brushes as described, for example, in U.S. Pat.Publication 2002/0065031A1 (Chou et al.), published May 30, 2002, thedisclosures of which are incorporated herein by reference.

One exemplary embodiment of a unitary brush according to the presentinvention is illustrated in FIG. 5. Referring to FIG. 5, cup brush 500has base 526 and bristles 528 attached at a right angle to base 526.Abrasive particles 530 are adhered to bristles 528 via binder 532according to the present invention. Base 526 has hole 534 in the centerthereof, which is threaded, for example, to allow for easy attachment toa rotary hand tool.

Another exemplary embodiment of a unitary brush according to the presentinvention is illustrated in FIG. 6. Referring to FIG. 6, radial brush600 has central hub base 603 having bristles 604 extending outwardlytherefrom. Central hub 603 has hole 607 in the center thereof. Bristles604 have abrasive particles 606 adhered thereto via binder 608 accordingto the present invention. Radial brushes according to the presentinvention may be used individually or ganged together.

To enhance the life of unitary brushes, binders according to the presentinvention that are in contact with bristles may have a flexural modulus,as measured according to ASTM Test Method D790-02 “Standard Test Methodsfor Flexural Properties of Unreinforced and Reinforced Plastics andElectrical Insulating Materials” (2002), that is similar to (e.g.,within 20 percent of) the flexural modulus of the bristles.

Curable compositions according to the present invention may be foamedand used to prepare foraminous abrasive articles as described in, forexample, U.S. Pat. No. 6,007,590 (Sanders), the disclosure of which isincorporated herein by reference.

Abrasive articles according to the present invention are useful forabrading a workpiece. Methods for abrading with abrasive articlesaccording to the present invention range from snagging (i.e., highpressure high stock removal) to polishing (e.g., polishing medicalimplants with coated abrasive belts), wherein the latter is typicallydone with finer grades (e.g., less ANSI 220 and finer) of abrasiveparticles. One such method includes the step of frictionally contactingan abrasive article (e.g., a coated abrasive article, a nonwovenabrasive article, or a bonded abrasive article) with a surface of theworkpiece, and moving at least one of the abrasive article or theworkpiece relative to the other to abrade at least a portion of thesurface.

Examples of workpiece materials include metal, metal alloys, exoticmetal alloys, ceramics, glass, wood, wood-like materials, composites,painted surfaces, plastics, reinforced plastics, stone, and/orcombinations thereof. The workpiece may be flat or have a shape orcontour associated with it. Exemplary workpieces include metalcomponents, plastic components, particleboard, camshafts, crankshafts,furniture, and turbine blades. The applied force during abradingtypically ranges from about 1 kilogram to about 100 kilograms.

Abrasive articles according to the present invention may be used by handand/or used in combination with a machine. At least one or both of theabrasive article and the workpiece is moved relative to the other whenabrading.

Abrading may be conducted under wet or dry conditions. Exemplary liquidsfor wet abrading include water, water containing conventional rustinhibiting compounds, lubricant, oil, soap, and cutting fluid. Theliquid may also contain defoamers, degreasers, and/or the like.

The present invention will be more fully understood with reference tothe following non-limiting examples in which all parts, percentages,ratios, and so forth, are by weight unless otherwise indicated.

EXAMPLES

Unless otherwise noted, all reagents used in the examples were obtained,or are available from, general chemical suppliers such as AldrichChemical Co., Milwaukec, Wis., or may be synthesized by known methods.

The following abbreviations are used throughout the Examples:

PU1 Ketoxime-blocked poly(1,4-butylene glycol) diisocyanate, 100% solidscommercially available under the trade designation “ADIPRENE BL-16” fromCrompton & Knowles Corporation, Stamford, Connecticut PU2Ketoxime-blocked poly(1,4-butylene glycol) diisocyanate, 85% solids inpropylene glycol monomethyl ether acetate commercially available underthe trade designation “ADIPRENE BL-31” from Crompton & KnowlesCorporation C1 A solution of 35 parts 4,4′-methylenedianiline in 65parts ethylene glycol monoethyl ether acetate C2Bis(4-amino-3,5-diethylphenyl)methane commercially available under thetrade designation “LONZACURE M-DEA” from Lonza AG, Werke, Switzerland S1Ethoxylated sorbitan ester commercially available under the tradedesignation “TWEEN 80” from Uniqema, New Castle, Delaware PAA 1 Acrosslinked copolymer of acrylic acid and long chain (C₁₀-C₃₀) alkylacrylates commercially available under the trade designation “PEMULEN1622” from Noveon, Cleveland, Ohio Lampblack Carbon black pigmentobtained under the trade designation “RAVEN 16” from Columbian ChemicalCompany, St. Louis, Missouri Silane Glycidoxypropyl trimethoxysilanecoupling agent (>60 percent by weight purity) obtained under the tradedesignation “Z-6040 SILANE” from Dow- Corning Corporation, Midland,Michigan LiSt Lithium stearate obtained under the trade designation“LITHIUM STEARATE 306” obtained from Witco Chemical Corporation, PerthAmboy, New Jersey, prepared and used at 44 percent by weight solids inpropylene glycol monomethyl ether acetate Solvent 1 Propylene glycolmonomethyl ether acetate obtained under the trade designation “ARCOSOLVPM ACETATE” from Arco Chemical Company, Houston, Texas Solvent 2 Xylene,ten degree from Ashland Chemical Company, Cranbury, New JerseyTensile Test

Tensile properties were evaluated according to ASTM Test Method D638-02, “Standard Test Method for Tensile Properties of Plastics”, thedisclosure of which is incorporated herein by reference, and which givesa comprehensive listing of tensile properties, testing procedures, andproperty calculations. Five Dumbbell-shaped specimens of dimensionsW=0.125 inch (3.8 mm)×LO=2.062 inches (52.4 mm)×WO =0.562 inch (14.3 mm)were die-cut from each film sample, where W is the width of the narrowsection of the dumbbell, LO is the overall length of the specimen, andWO is the overall length of the specimen. Each dumbbell was clamped intoa constant rate of extension tensile testing machine having the tradedesignation “SINTECH 2 ” and equipped with a 200 lb load cell availablefrom MTS Systems Corporation, Cary, N.C. Data acquisition, tensileproperty calculations, and machine control was performed using softwareavailable from MTS Systems Corporation, Cary, N.C. under the tradedesignation “TESTWORKS VERSION 2.1”. The gage length was 1.0 inch (2.54cm), the strain rate was set to 1.0 inch/minute (2.54 cm/min), and thespecimen gripping surface was serrated and 2 inches (5 cm) wide×1.5inches (3.8 cm) long. Test results reported are the statistical averageof 10 measurements of a single film.

General Method for Film Preparation—Friction Test

Films for subsequent friction testing were prepared on steel plates(phosphate coated, 4 inches×12 inches×0.030 inch (10.1×30.5 cm×0.76mm)). Each film was prepared by knife coating the specified compositionat a wet thickness of 0.010 inch (0.25 mm), allowing it to air dry for 2hours, and then placing it in a convection oven at 250 ° F. (121 ° C.)for 18 hours. Each film was then allowed to cool to room temperatureprior to friction measurements at various temperatures.

Friction Test

Coefficients of friction were determined using a Thwing-AlbertFriction/Peel Tester Model No. 225-1 (Thwing-Albert Instrument Company,Philadelphia, Pa.) that was equipped with a 2000-gram load cell and avariable temperature platen cooled to 15 ° C.). Measurements were madeby pulling a steel bar weighing 500 grams (g) and having a 2 inch×2 inch(5.1 cm×5.1 cm) sliding contact face across a film specimen at 2.1inches/min (5.6 cm/min). Three measurements of coefficient of staticfriction (i.e., SF), and coefficient of kinetic friction (i.e., KF),were made for each specimen and reported as an average value.

Cut and Wear Test

Abrasive articles comprising the inventive compositions were testedaccording to the Cut and Wear test. Each test specimen consisted ofthree 10-inch (25.4 cm) diameter discs with 2-inch (5.08 cm) diametercenter holes that were cut from the nonwoven abrasive article to betested. The three discs were mounted on a 2-inch (5.08) diameter drivenshaft with spacers (6 inches (15.24 cm) outer diameter×2 inches (5.08cm) inner diameter×½ inch (1.27 cm) thick) between each pair of discs.Three such test specimens were prepared for each nonwoven abrasivearticle to be tested. Each test specimen was evaluated for abrasivenessagainst an 11 inch (28 cm)×4 inch (10 cm)×0.056 inch (1.4 mm) perforatedcarbon steel screen workpiece ( 5/32 inch (0.40 cm) hole diameter on7/32 inch (0.56 cm)) centers staggered pattern on 1008 cold rolledsteel, stock pattern 401 obtained from Harrington & King Company,Chicago, Ill. Test specimens were rotated at 6000 ft/min (1829 m/min)and urged against a workpiece at 20 psi (0.14 MPa) force for one minute.A new workpiece was mounted and the abrading cycle was repeated. Thebefore-test weight and the after-test weight of both the test specimenand the two workpieces were recorded. Test specimen weight loss wasrecorded as “wear”. The combined weight loss of both workpieces wasrecorded as “cut”.

EXAMPLES 1-8 and COMPARATIVE EXAMPLES A-D

The compositions of Examples 1-8 and Comparative Examples A-D wereprepared by combining, in the amounts indicated in Table 1 (below), PU1and solvent borne curative (i.e., C1 or C2 dissolved in Solvent 1),which were stirred until completely dissolved, then nonionic surfactant(S1) and/or crosslinked copolymer (PAA 1), if specified, were finallyadded.

TABLE 1 COMPOSITION, parts per hundred (weight basis) EXAMPLE PU1 C1 C2Solvent 1 S1 PAA 1 COMPARATIVE A 72.4 25.0 0 0 0 0 COMPARATIVE B 72.425.0 0 0 0.8 0 1 72.4 25.0 0 0 0.8 0.3 2 72.4 25.0 0 0 0 0.3 3 72.4 25.00 0 0 3.0 4 72.4 25.0 0 0 0 15.0 COMPARATIVE C 72.4 0 13.8 7.3 0 0COMPARATIVE D 72.4 0 13.8 7.3 0.9 0 5 72.4 0 13.8 7.3 0.9 0.3 6 72.4 013.8 7.3 0 0.3 7 72.4 0 13.8 7.3 0 3.0 8 72.4 0 13.8 7.3 0 15.0

Films were prepared from the compositions of Examples 1-8 andComparative Examples A-D according to the General Method for FilmPreparation—Friction Test, and test specimens of the prepared films wereevaluated according to the Friction Test. Friction Test results areshown in Table 2 (below).

TABLE 2 AVERAGE COEFFICIENT TEMPERATURE, OF FRICTION EXAMPLE ° F. (° C.)SF KF Comparative A 60 (16) 1.003 0.980 Comparative B 60 (16) 0.6420.586 1 60 (16) 0.358 0.290 2 60 (16) 0.320 0.281 3 60 (16) 0.357 0.2744 60 (16) 0.312 0.251 Comparative A 150 (66)  0.582 0.549 Comparative B150 (66)  0.354 0.313 1 150 (66)  0.421 0.305 2 150 (66)  0.439 0.373 3150 (66)  0.464 0.326 4 150 (66)  0.382 0.284 Comparative A 225 (107)0.533 0.469 Comparative B 225 (107) 0.318 0.299 1 225 (107) 0.374 0.2482 225 (107) 0.323 0.216 3 225 (107) 0.300 0.224 4 225 (107) 0.238 0.198Comparative A 300 (149) 0.488 0.481 Comparative B 300 (149) 0.346 0.3271 300 (149) 0.425 0.271 2 300 (149) 0.346 0.315 3 300 (149) 0.349 0.2284 300 (149) 0.244 0.186 Comparative C 60 (16) 1.056 0.984 Comparative D60 (16) 0.959 0.929 5 60 (16) 0.509 0.464 6 60 (16) 0.504 0.528 7 60(16) 0.329 0.229 8 60 (16) 0.296 0.223 Comparative C 150 (66)  0.9670.938 Comparative D 150 (66)  0.816 0.796 5 150 (66)  0.427 0.409 6 150(66)  0.386 0.364 7 150 (66)  0.330 0.232 8 150 (66)  0.265 0.202Comparative C 225 (107) 0.637 0.610 Comparative D 225 (107) 0.559 0.5085 225 (107) 0.307 0.280 6 225 (107) 0.277 0.225 7 225 (107) 0.235 0.1728 225 (107) 0.236 0.144 Comparative C 300 (149) 0.489 0.493 ComparativeD 300 (149) 0.471 0.468 5 300 (149) 0.286 0.249 6 300 (149) 0.248 0.1727 300 (149) 0.191 0.144 8 300 (149) 0.229 0.136

EXAMPLES 9-12 and COMPARATIVE EXAMPLES E-H

A continuous filament nonwoven web was made according to the procedureof Example 1 of U.S. Pat. No. 4,227,350 (Fitzer), the disclosure ofwhich is incorporated herein by reference. Polycaprolactam (availablecommercially under the trade designation “ULTRAMID B3 ” from BASFCorporation, Polymers Division, Mount Olive, N.J.) was extruded at apressure of 2800 psi (19 MPa) through a 60-inch (1.5 meter) longspinneret nominally having 2890 counter sunk, counter bored openingsarranged in eight equal rows spaced 0.080 inch (0.2 cm) apart in ahexagonal close packed array, each opening having a diameter of 0.016inch (0.4 mm), and having a land length of 0.079 inch (2.0 mm). Thespinneret was heated to about 248° C. and positioned 12 inches (30 cm)above the surface of a quench bath, which was continuously filled andflushed with tap water at the rate of 0.5 gallon per minute (2liters/min). Filaments extruded from the spinneret were permitted tofall into the quench bath, where they undulated and coiled between two4-inch (10 cm) diameter by 60-inch (1.5 m) long smooth-surfaced rolls.Both rolls were positioned in the bath with their axes of rotation about2 inches (5 cm) below the surface of the bath, and the rolls wererotated in opposite directions at a rate of about 9 ft/min (2.7 m/min)surface speed. The rolls were spaced to lightly compress the surfaces ofthe resultant extruded web, providing a flattened surface on both sides.The polycaprolactam was extruded at a rate of about 700 pounds per hour(320 kg/hr), producing a web that was 59 inches (1.5 m) wide×0.66 inch(17 mm) thick. The web had eight rows of coiled, undulated filaments.The resulting coiled web had a basis weight of 14.2 grams/24 squareinches (0.875 kg/m²), and had a void volume of 92.6 percent by volume.The filament diameter averaged about 15 mils (0.38 mm). The web wascarried from the quench bath around one of the rolls and excess waterwas removed from the web by drying at room temperature (i.e., 20 ° C. to24° C.) using forced air.

The nonwoven web prepared above was used to make Examples 9-12 andComparative Examples E-H by sequentially applying a make coat, mineralcoat, and size coat, as described below.

A make coat, obtained by combining the ingredients shown in Table 3(below), was applied to the nonwoven web using a 2-roll coater.

TABLE 3 Comparative Comparative Comparative Comparative Example E,Example Example F, Example Example Example G, Example H, ExampleComponent parts 9, parts parts 10, parts 11, parts parts parts 12, partsC1 — — 25.0 25.0 25.0 25.0 — — C2 13.8 13.8 — — — — 13.8 13.8 PU1 72.472.4 72.4 72.4 72.4 72.4 72.4 72.4 S1 — — 0.8 — 0.8 — 0.9 0.9 PAA 1 —0.3 — 0.3 0.3 — — 0.3 Solvent 1 7.3 7.3 — — — — 14 14

The indicated make coat was applied at a dry add-on weight of 6.5 g/24in² (0.420 kg/m²). Grade 36 SiC abrasive granules (2.6 kg/m²) were thenapplied to the coated web via a drop coater. The web was agitated toencourage penetration of the granules into the interstitial spaces ofthe web. The particle-coated web was then heated by passing it through a90 ft (27 m) long oven. A size coat consisting of 9.6 parts C1, 27.5parts PU1, 27.5 parts PU2, 1.2 parts lampblack, 0.7 parts silane, 19.3parts Solvent 2, and 4.7 parts LiSt was then sprayed on the upper sideof the web, which was then heated in an oven. The web was inverted andthe other side was sprayed with an identical amount of the size coatingand heated in an oven under the same conditions. The final size coat dryadd-on was 7.78 g/24 in² (0.503 kg/m²). Discs ((10-inch (25.4mm) outerdiameter, 2-inch (5.1mm) inner diameter) were cut from the resultingnonwoven abrasive articles and were tested according to the Wear Test.Curing conditions used for the make and size coatings, and Wear Testresults are reported in Table 4 (below).

TABLE 4 NUMBER OF MAKE COAT MAKE COAT MAKE COAT SIZE COAT SIZE COAT CURETEMP, LINE SPEED, OVEN CURE TEMP, LINE SPEED, WEAR, CUT, EXAMPLE ° C.ft/min (m/min) PASSES ° C. ft/min (m/min) g/2 min g/2 min Comparative165 10 (3.0) 1 160 10 (3.0) 33.6 18.39 Example E  9 165 10 (3.0) 1 16010 (3.0) 44.2 22.52 Comparative 165 10 (3.0) 1 160 10 (3.0) 72.9 21.43Example F 10 165 10 (3.0) 1 160 10 (3.0) 72.8 22.42 11 165 10 (3.0) 1160 10 (3.0) 84.5 23.03 Comparative 165 10 (3.0) 1 160 10 (3.0) 83.321.79 Example G Comparative 165 10 (3.0) 1 160 10 (3.0) 44.8 23.2Example H 12 165 10 (3.0) 1 160 10 (3.0) 53.4 25.1

Various modifications and alterations of this invention will becomeapparent to those skilled in the art without departing from the scopeand spirit of this invention, and it should be understood that thisinvention is not to be unduly limited to the illustrated embodiments setforth herein.

1. A curable composition comprising: blocked polyisocyanate; curative;and a crosslinked copolymer of monomers comprising at least onefree-radically polymerizable carboxylic acid and at least one of analkyl or alkaryl(meth)acrylate, wherein at least one of the alkyl oralkaryl (meth)acrylate has from 11 carbon atoms to 34 carbon atoms, andwherein the amount of crosslinked copolymer is in a range of from 1percent by weight to 20 percent by weight, based on the total weight ofthe composition.
 2. A curable composition according to claim 1, furthercomprising organic solvent.
 3. A curable composition according to claim1, wherein the monomers comprise acrylic acid.
 4. A curable compositionaccording to claim 1, wherein the monomers comprise acrylic acid and analkyl acrylate, further wherein the alkyl acrylate has from 13 carbonatoms to 33 carbon atoms.
 5. A curable composition according to claim 1,wherein the blocked polyisocyanate comprises a compound having theformula:

wherein n is an integer greater than or equal to
 1. 6. A curablecomposition according to claim 1, wherein the curative comprises atleast one of bis(4-amino-3-ethylphenyl)methane orbis(4-amino-3,5-diethylphenyl)methane.
 7. A curable compositionaccording to claim 1, further comprising an additive selected from thegroup consisting of a filler, a lubricant, an antistatic agent, agrinding aid, and a colorant.
 8. A method for making a curablecomposition comprising mixing components comprising: blockedpolyisocyanate; curative; and a crosslinked copolymer of monomerscomprising at least one free-radically polymerizable carboxylic acid andat least one of an alkyl or alkaryl (meth)acrylate, wherein at least oneof the alkyl or alkaryl(meth)acrylate has from 11 carbon atoms to 34carbon atoms, and wherein the amount of crosslinked copolymer is in arange of from 1 percent by weight to 20 percent by weight, based on thetotal weight of the composition.
 9. A method according to claim 8,wherein the components further comprise abrasive particles.
 10. A methodaccording to claim 8, wherein the components further comprise organicsolvent.
 11. A composition according to claim 8, wherein the monomerscomprise acrylic acid and an alkyl acrylate, further wherein the alkylacrylate has from 13 carbon atoms to 33 carbon atoms.
 12. A methodaccording to claim 8, wherein the blocked polyisocyanate comprises acompound having the formula:

wherein n is an integer greater than or equal to
 1. 13. A methodaccording to claim 8, wherein the curative comprises at least one ofbis(4-amino-3-ethylphenyl)methane orbis(4-amino-3,5-diethylphenyl)methane.
 14. A composition according toclaim 8, further comprising an additive selected from the groupconsisting of a filler, a lubricant, an antistatic agent, a grindingaid, and a colorant.
 15. An abrasive article comprising abrasiveparticles and a polymerized reaction product of a curable compositioncomprising: blocked polyisocyanate; curative; and a crosslinkedcopolymer of monomers comprising at least one free-radicallypolymerizable carboxylic acid and at least one of an alkyl or alkaryl(meth)acrylate, wherein at least one of the alkyl oralkaryl(meth)acrylate has from 11 carbon atoms to 34 carbon atoms, andwherein the amount of crosslinked copolymer is in a range of from 1percent by weight 20 percent by weight, based on the total weight of thecomposition.
 16. A method according to claim 15, wherein the componentsfurther comprises abrasive particles.
 17. A method according to claim15, wherein the components further comprise organic solvent.
 18. Amethod according to claim 15, wherein the monomers comprise acrylicacid.
 19. A method according to claim 15, wherein the monomers compriseacrylic acid and an alkyl acrylate, further wherein the alkyl acrylatehas from 13 carbon atoms to 33 carbon atoms.
 20. A method according toclaim 15, wherein the blocked polyisocyanate comprises a compound havingthe formula:

wherein n is an integer greater than or equal to 1 .
 21. A methodaccording to claim 15, wherein the curative comprises at least one ofbis(4-amino-3-ehtylphenyl)methane orbis(4-amino-3,5-diethylphenyl)methane.
 22. A method according to claim15, further comprising an additive selected from the group consisting ofa filler, a lubricant, an antistatic agent, a grinding aid, and acolorant.